Frank: the fantasy album

The best Sinatra album ever. What would it consist of? A songwriting compendium. An essay in swing. And Frank's own story. He's 80 on Tuesday. Here it is. By Richard Cook

Time After Time (1946)

Some have said that the hallmark of great singers is the way they're able to elevate indifferent material to some kind of greatness. Perhaps it's truer to say that one can tell the great singers by how well they handle the greatest songs: they're never dwarfed by the material, never anything less than its master.

"Time After Time" was written by Jule Styne and Sammy Cahn for the movie musical It Happened in Brooklyn, and it might be the finest of their many collaborations. Sinatra may have looked like a skinny, scrawny type with an absurd curl in his hair. But when you put his records on, you heard an American sound so captivating that it hastened the death of the big bands with which the singer began. His first great period. It didn't last long.

I'm a Fool to Want You (1951)

It's all too tempting to hear this piece of art as a direct imitation of life: Sinatra was facing up to a marriage on the rocks, a career on the skids and a place to go that looked like nowhere at all. At Columbia, where he had spent eight years, his star was descending even faster than those of the big bands he'd grown up with. The company's notorious A&R man, Mitch Miller, was obliging him to make records with dog impersonators and his movie career had stalled. In March 1951, he had barely a year left before Columbia dumped him. The faithful Axel Stordahl was still in the conductor's chair, and he leads the orchestra through an arrangement that seems to tremble ominously beneath the singer's fixed stare of resignation. The song is an eerie meditation on the loneliness of erotic obsession, a man telling himself how pitiful he is, while unable to do anything about it.Sinatra gives his all. The racked intensity of this performance is unsurpassed in Sinatra's output, and a rare instance of the artist as naked as he would ever allow himself to be.

In the Wee Small Hours of the Morning (1955)

It's such a lovely, lonely melody and it suits exactly the glad-to-be- unhappy kind of lyric that goes with it. Sinatra had signed to Capitol after Columbia, had struck movie gold with From Here to Eternity, and had remodelled a singing persona which moved seamlessly from faded bobbysox idol to worldly-wise man. This was the title tune from his third album for Capitol, and it ushered in a new era for "The Voice". The lovely bel canto tenor had grown darker, extra gravitas displacing the limberness of youth.

I Thought About You (1956)

An irony that Sinatra should record the album which most personified the values of the swing-era singer on the eve of rock 'n' roll's outbreak. Still, admirers of Songs for Swingin' Lovers have the last laugh. It has endured as well as any long-player of the past 40 years. Nelson Riddle, the most perspicacious of arrangers, struck the balance which typified Sinatra's singing: somewhere between out-and-out emoting and a certain craftsmanlike detachment. With Billy May, Sinatra would belt out the material against flaring brass and reeds, but with Riddle he could relax and breeze through it. There's something special about "I Thought About You". Johnny Mercer's lyric sets up the narrative from the first line - "I took a trip on a train, and I thought about you". Sinatra muses lazily over the words but hits the denouement exactly right: "What did I do? I thought about you".

Come Fly With Me (1957)

Every public-bar singer has had a go at "My Way" and saloon crooners are murdering "New York, New York" to this day, but has anyone else ever really touched "Come Fly With Me"? In his later performing years, Sinatra always started his shows with this one, as often as not foreshortening the opening line into a simple "Fly with me", the words gusting in from nowhere. The original album artwork suggests a vanished world of mysterious, romantic TWA travel, in the days before frequent-flyer programmes, and the swinging delivery is a textbook lesson in getting a song airborne.

What's New? (1958)

Bob Haggart's tune has been a favourite with jazz improvisers for many years. Sinatra gives it a palpable sense of Pagliacci loneliness. Frank liked to play-act through some of his material, the best instance being the deathless but somewhat contrived routine for "One for My Baby and One More for the Road". In this more subtle portrait, where a gentleman meets an old flame and admits, in the final breath, that it hasn't flickered out as far as he's concerned, the singer finesses an ancient ache into something tender and beautiful.

I'm Getting Sentimental Over You (1961)

It's difficult to fathom what Sinatra's relationship with jazz is. Like every singer of his generation, he had to follow Louis Armstrong and Bing Crosby, who between them changed the way every pop singer sang; and he made his name first as band singer for another holdover from the jazz age, trombonist Tommy Dorsey. Yet Sinatra has never seemed like a jazz singer: he won't scat, he lets the orchestra swing rather than doing it himself, and his phrasing seems to glide over the beat rather than search out the improvisational freedoms of jazz. Still, this version of what was Dorsey's theme song exposes in subtle ways what jazz did for Sinatra. He learned from Dorsey how to master long-breathed phrasing, and that skill informed his work at both slow and fast tempos for the rest of his career. In this handsome interpretation of a song that few have recorded since, Sinatra pays exemplary tribute.

I Get a Kick Out of You (1962)

There has to be some representation of Sinatra the boor. Sometimes he'll manhandle songs as readily as he will caress them, and sometimes the composer won't much like it. Larry Adler remembers how Sinatra invited Cole Porter to an after-hours performance, where he sang this song and changed the key line to "I get a boot out of you". Porter left and sent a message to the effect that if he couldn't sing the songs the way they were, he should leave them alone. Frank makes a couple of lyric changes here too, on a bouncy big-band treatment by Neal Hefti, but it's a classy piece of high-stepping.

If I Had You (1962)

Robert Farnon is a big, jolly man whose unassuming guile has squeezed the best out of orchestras and singers for 40 years. He arranged Sinatra's one British recording session with his customary aplomb. Great Songs from Great Britain found Sinatra in Bayswater on three hot nights in June 1962, cutting a dozen songs by British hands. There are lovely versions of "A Nightingale Sang in Berkeley Square" and "The Very Thought of You", but this charming composition finds the man at his most wistfully beguiling. Benny Green remembers how, after one difficult take on the session, Sinatra redid the tune perfectly and remarked to the studio: "See what you get when you keep good hours and live a clean life."

I Have Dreamed (1963)

One of the most perfect of all Sinatra's records. Nelson Riddle turns in his grandest, most sweeping arrangement of the finest song from The King and I, an almost mystical meditation on a love that may or may not be unrequited. Sinatra could have cruised through it and done a merely excellent job, but Riddle recalled that he'd never seen the singer so concentrated as he was on this session. As one line follows another, each word precisely placed in the flow, one can hear a definitive interpretation falling into place. By the end, where the voice rises to meet the noble climax, there seems to be no other way for this song to ever be sung again.

It Was a Very Good Year (1965)

Sinatra turned 50 in 1965 and celebrated the fact by releasing an album of maudlin and mildly phoney "reminiscences" called The September of My Years. Gordon Jenkins returned to helm the project, and amidst some frightful stuff was this creepy masterpiece. It was written by the otherwise little- known Ervin Drake, and seems tailor-made for the great man's most solipsistic outlook. He remembers small-town girls whose "hair came undone when I was 21" and the like - and as a weary, slightly ironic memoir of a middle- aged rogue, it's hard to beat.

A Long Night (1981)

Late-period Sinatra is fraught with difficulties. Mistaken choices of material, hack arrangements, footling album concepts, and the unavoidable deterioration of the voice - one has to tread carefully among all the albums of the Seventies and Eighties. Nothing from the recent, frightful Duets albums qualifies as a worthy goodbye, but this earlier tune surely does. Sinatra always did well with Alec Wilder songs: there was a fine "I'll be Around" on In the Wee Small Hours, and a spellbinding version of a song nobody else has even considered, "Where Do You Go?", on No One Cares. And then there's this, a composition Wilder and Loonis McGlohan came up with for She Shot Me Down, probably the last great Sinatra album. Wilder's tart eloquence fits the singer's penchant for man-alone ponderings just as Gordon Jenkins's arrangement underscores it. Sinatra sounds old, heavy and weary - and makes a virtue out of all three. As the performance moves to its chilling final line - "No daylight, just a long night for me" - it becomes a valediction for Wilder, Jenkins and Sinatra alike. A great one, too.